Cyanogen Bromide → HCID 86626276, compound

HRID 1097551Notes

Reaction equation

HRID 1097551 reaction equation
[N:1]#[C:2][Br:3].[NH2:4][C:5]1[C:6]([Cl:21])=[N:7][C:8]2[C:13]([C:14]=1[NH:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])=[CH:12][CH:11]=[CH:10][CH:9]=2>C(O)C>[BrH:3].[Cl:21][C:6]1[C:5]2[N:4]=[C:2]([NH2:1])[N:15]([CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 226726541-((3-Amino-2-chloroquinolin-4-yl)amino)-2-methylpropan-2-ol

Product 1

HCID 86626276HCID 86626276, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyanogen bromide (4.78 g, 45.2 mmol) was added to a solution of 1-[(3-amino-2-chloro-4-quinolinyl)amino]-2-methyl-2-propanol (André et al, U.S. Pat. No. 4,988,815, Example 13, 10.0 g, 37.6 mmol) in ethanol (200 mL), and the solution was heated overnight at 90° C. and allowed to cool to ambient temperature. A precipitate formed and was isolated by filtration, washed once with diethyl ether, and then washed several times with dichloromethane to provide 9.28 g of 1-(4-chloro-2-amino-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol hydrobromide as a gray powder.

Workup

  1. customA precipitate formed
  2. customwas isolated by filtration
  3. washwashed once with diethyl ether
  4. washwashed several times with dichloromethane

Sources & evidence

ORD record
ord-8fd84e7ba845442ba836dcfddb499c11
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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